Historical clue formulations

• Word with failure or terror — 2024-06-21
• The absolute worst — 2016-11-10
• Showing hopelessness — 2014-08-27
• Utterly hopeless — 2013-08-07
• Utterly hopeless — 2013-02-11
• Sorry — 1999-06-25
• Utterly miserable — 1994-04-08